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Mark Penn made a name for himself in Washington by bulldozing enemies of the Clintons. Now he spends his days trying to do the same to Google, on behalf of archrival Microsoft.

Since Penn was put in charge of “strategic and special projects” at Microsoft, much of his job has involved efforts to trip up Google. Drawing on his background in polling, data crunching and campaigning, Penn created a holiday commercial in which Microsoft criticises Google for polluting the quality of its shopping search results with advertisements.

“Don’t get scroogled,” it warns.

His other projects include a blind taste test, Coke-versus-Pepsi style, of search results from Google and Microsoft’s Bing.

The campaigns by Penn, 58, a longtime political operative known for his brusque personality and scorched-earth tactics, are part of a broader effort at Microsoft to give its marketing the nimbleness of a political campaign. They are also a sign of the company’s mounting frustration with Google after losing billions of dollars a year on its search efforts, while losing ground to Google in the browser and smartphones markets.

The fruits of its recent work in this area could come out soon, when the Federal Trade Commission is expected to announce the results of its antitrust investigation of Google.

But Microsoft, has realised that it cannot rely only on regulators to scrutinise Google—which is where Penn comes in.

Jill Hazelbaker, a Google spokeswoman, declined to comment on Microsoft’s actions specifically but said that while Google also employed lobbyists and marketers, “our focus is on Google not the competition.”

In Washington, Penn is a lightning rod. He developed a relationship with the Clintons as a pollster during President Bill Clinton’s 1996 re-election campaign, when he helped identify the value of “soccer moms” and other niche voter groups.

As chief strategist for Hillary Clinton’s unsuccessful 2008 campaign for president, he conceived the “3 a.m.” commercial that raised doubts about whether Barack Obama, then a senator, was ready for the Oval Office.

But his approach has ended up souring many of his professional relationships. He left Clinton’s campaign after an uproar about his consulting work for the government of Colombia, which was seeking the passage of a US trade treaty that Clinton, then a senator, opposed.

Hiring Penn demonstrates how seriously Microsoft is taking this fight, said Michael A. Cusumano, a business professor at MIT. “They’re pulling out